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Risky Business (1983)

Ecstatic when his parents leave on vacation for a few days, high school senior Joel Goodsen (Tom Cruise) cuts loose with his best friend Miles. After an attempt at securing the services of a prostitute goes slightly awry, Joel hires gorgeous Lana (Rebecca De Mornay) for a night of delight. Stunned by the amount of Lana’s “bill” the next morning, Joel grows frantic after he crashes his father’s Porsche. In an effort to raise lots of money fast, a desperate Joel turns the house into a brothel.

Valley Girl (1983)

Lovely teen Julie Richman (Deborah Foreman) is steeped in the excessive, pink-clad culture of the San Fernando Valley, complete with her narcissistic boyfriend, Tommy (Michael Bowen). At a party, however, Julie falls for an edgy Hollywood punk named Randy (Nicolas Cage), and the two begin an unlikely romance. Torn between fitting in with her superficial friends and embracing a more non-conformist lifestyle, Julie ultimately has to decide to stay with Tommy or take a risk with Randy.

Clueless (1995)

Shallow, rich and socially successful Cher (Alicia Silverstone) is at the top of her Beverly Hills high school’s pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai (Brittany Murphy) a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother (Paul Rudd) was right about how misguided she was — and falls for him.